On the afternoon of May 9, the U.S. attorney general and the Soviet spy sat together on a park bench on Constitution Avenue, near the Justice Department. “Look here, Georgi, I know pretty well about your standing and your connections with the boys in Khrushchev’s entourage,” Bolshakov later recalled RFK saying, according to Richard Reeves’s biography “President Kennedy: Profile in Power.” “I think they wouldn’t mind getting truthful firsthand information from you, and I presume they’ll find a way of passing it on to Khrushchev.”

The president’s brother and the short, tubby Russian spy met dozens of times over the next 18 months. The Kennedys had been warned against relying on the bureaucrats at the State Department by their father, who felt he had been undone by professional diplomats during his rocky tenure as ambassador to Britain at the beginning of World War II. JFK viewed State as slow-moving and lightweight. “They’re not queer, but, well, they’re sort of like Adlai,” he said, referring to Adlai Stevenson, the U.S. ambassador to the United Nations.

Bobby was not particularly articulate, and the Russians sometimes did not understand him. The president’s brother was also remarkably indiscreet. He told the GRU agent that the U.S. Joint Chiefs of Staff had “offered the president a report in which they confirmed that the United States is currently ahead of the Soviet Union in military power and that in extremis it would be possible to probe the forces of the Soviet Union.” Kennedy’s loose use of the word “probe” set off alarm bells in the Kremlin. Did he mean the Pentagon was contemplating a preemptive strike?